Dorchester Cottage Holidays

Your search returned 99 cottages.

All cottages available for only £20 Deposit!*

For a limited time only, all our cottages can be reserved for only £20 Deposit. Don't miss out!

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    • Sleeps4
    • Bedrooms2
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    Luxury barn conversion in Charminster. Quality accommodation with beams and en-suites. Adjacent golf course. Excellent w... (Ref. 1440)

    7 nights from £425.49

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    • Sleeps6
    • Bedrooms3
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    A grade II listed converted school near the town of Dorchester in Dorset. En-suite. Exposed wooden beams. Dorchester 3 miles. (Ref. 930956)

    7 nights from £504.49

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    • Sleeps4
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    Gorgeous, semi-detached, Grade II listed 17th century thatched cottage in the Dorset village of Upwey. Quality accommoda... (Ref. 916915)

    7 nights from £403.49

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    • Sleeps2
    • Bedrooms1
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    Cosy, detached stone cottage, in Dorset village of Upwey. Elevated site, lovely rural views. Eaves bedroom, conservatory... (Ref. 943806)

    7 nights from £308.49

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    • Sleeps5
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    A charm-filled terraced cottage set in the stunning village of Upwey in Dorset. Pet-friendly. Dorset AONB. Weymouth 4 miles. (Ref. 972855)

    7 nights from £375.49

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    A beautiful terraced holiday home, one of five set around a courtyard, on the edge of Upwey, near Weymouth. Attractive, ... (Ref. 932159)

    7 nights from £394.49

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    Stunning semi-detached holiday cottage in courtyard setting, on the edge of Upwey, near Weymouth. Very high standard of ... (Ref. 932158)

    • 10% off - Fri 27th Apr to 11th May 2018

    7 nights from £438.49

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    • Sleeps4
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    Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weym... (Ref. 932157)

    7 nights from £438.49

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    • Sleeps6
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    Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weym... (Ref. 932161)

    • 10% off - Fri 13th Apr to 18th May 2018

    7 nights from £489.49

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    • Sleeps6
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    A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. En-suite, modern features.... (Ref. 932160)

    • 10% off - Fri 18th May to 25th May 2018

    7 nights from £489.49

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All cottages available for only £20 Deposit!*

For a limited time only, all our cottages can be reserved for only £20 Deposit. Don't miss out!

*Applicable to holidays commencing at least 6 weeks in the future. Full balance due 6 weeks prior to departure. Please refer to £20 deposit offer terms & conditions for further information.

Just show me Dorchester Cottages

If you're looking for somewhere with facilities on hand yet close to amazing countryside, our Dorchester cottages make great contenders. Think elegant architecture, historic sites, thriving culture and excellent shopping.

Dorchester's a fantastic place for browsing. Shoppers will find all kinds of specialist shops, high street names and markets, while museums range from dinosaurs, teddies and Chinese Terracotta Warriors, to Roman artefacts and Tutankhamun. And in between shopping and sightseeing, relish delicious snacks and meals in a wide variety of establishments, from pavement cafes to Michelin-starred restaurants.

When it comes to historic sites, Dorchester features a treasure trove of delights. Don't miss the splendid Roman Town House, the home of infamous 'Hanging' Judge Jeffreys, the huge Iron Age hill fort of Maiden Castle and the Roman amphitheatre at Maumbury Rings.

Thomas Hardy's Wessex a stone's throw from your Dorchester cottage

Dorset's wonderful landscapes have inspired many writers and most of Hardy's novels are based on Dorset; Dorchester is indeed the legendary town of 'Casterbridge'. The Dorset County Museum displays his works, while you can also visit his birthplace Hardy's Cottage and his Victorian villa Max Gate, designed by Hardy and built by his brother. Discover more of his beloved 'Wessex' on foot and stride out from your Dorchester cottage along the Dorchester to Weymouth Trail (10 miles).

To the west of the town centre you'll find Poundbury, Prince Charles' award-winning residential development built in the traditional architectural style of Dorchester and home to a variety of attractions, including a monthly farmers' market.